TW201436809A - Composition and process for semi-permanent straightening of the hair - Google Patents

Abstract

The present invention provides a hair straightening composition with improved ease of use and reduced smoke development during the application of a straightening iron. The composition comprises at least one carboxylic acid of the formula (I) in combination with at least one polymeric thickening agent selected from non-ionic, anionic, cationic and amphoteric polymers having a viscosity of at least 500 mPa.s measured at a polymer concentration of 1% by weight, in water and at 20 DEG C with a Brookfield viscometer: R-CO-COOH Formula (I) In further aspects, the present invention concerns a process for semi-permanent straightening of the hair, utilizing said composition, the use of the composition for straightening hair, and a kit comprising the composition and a straightening iron.

Description

Composition and method for semi-permanent straightening of hair

This invention relates to compositions and methods for semi-permanent straightening of hair.

A known method for straightening a curled or rolled hair involves the use of a straightening iron. The high temperature of the hair iron causes the hydrogen bonds in the keratin of the hair to break, thereby achieving temporary straightening. The hydrogen bond is again formed by the action of moisture, so that the hair returns to its original shape with time due to the humidity of the air, and the straightening effect disappears after washing the hair.

The shape of the hair is largely determined by the disulfide bond of the two cysteine portions of the bound hair keratin. In order to achieve a more permanent setting of the hair, the known method involves breaking the disulfide bond by the action of a reducing agent containing a sulfide or a sulfur group. After the hair has been formed into the desired shape, a new disulfide bond is formed by applying an oxidizing agent such as hydrogen peroxide to fix the shape of the hair. However, the use of such agents can cause damage to the hair.

As an example of such hair styling treatment, reference is made to GB 1 416 564 which describes a reducing composition comprising thioglycolate or thiol lactate as a reducing agent and a fixing composition comprising hydrogen peroxide as an oxidizing agent. The reducing composition may further comprise a salt such as an acid of glyoxylic acid as a buffer.

As an alternative to the two-step reduction method and the oxidation method described above, the disulfide bridge can be decomposed by the action of an alkali agent such as sodium hydroxide at a pH of about 11 or higher. Under these conditions, the disulfide (or cystine) moiety can undergo a disproportionation reaction during the elimination of sulfur. And it is decomposed into an α-β-unsaturated dehydro-alanine moiety and a cysteine moiety. After the hair has been formed into the desired shape, the dehydrogenation-alanine moiety and the cysteine moiety form a thioether bond and are combined into lanthionine to stabilize the straightened state of the hair. Since the disulfide or cystine moiety is converted to the lanthione moiety, such hair straightening using an alkaline agent is also known as lanthionization.

Both the two-stage reduction/oxidation process and the lanthionelation process rely on the cleavage of disulfide bonds in the hair protein and the formation of new bonds, resulting in irreversible changes in the shape of the hair. This means that these methods achieve permanent straightening in which the treated portion of the hair maintains its shape and the straightening effect only disappears due to the growth of the hair.

Recently, it has been found that a carboxylic acid having a carbonyl group adjacent to a carboxyl group (such as glyoxylic acid), which is called a buffer in a cosmetic composition, can have a semi-permanent straightening effect when used in combination with a mechanical straightening method.

In this regard, WO 2011/104282 describes a method for semi-permanent hair straightening which involves applying a composition comprising alpha-keto acid to the hair, allowing the composition to contact the hair for 15 to 120 minutes, drying the hair and Pull straight hair at a temperature of 200 ± 50 ° C by straightening the hair iron.

Furthermore, WO 2012/010351 describes a treatment for the semi-permanent straightening of crimped, rolled or wavy hair at a temperature of 200 ± 30 ° C using a straightening iron by applying a glyoxylic acid solution in combination with a mechanical straightening. After treatment, the hair is said to retain its shape for at least six consecutive washes.

EP 0 685 219 describes a composition suitable for use as a pretreatment agent for hair after subjecting to perm wave treatment, the composition comprising a film-forming cationic, anionic and/or amphoteric polymer, an amphoteric surfactant, an organic acid and a C2 to C4 alcohol, It does not contain a cationic surfactant.

The present invention provides a hair straightening composition having a pH of 4 or less and comprising the following: - at least one carboxylic acid of the formula (I) and/or its hydrate and/or its salt in a total concentration of from 0.1 to 40% by weight based on the total weight of the composition: R-CO-COOH Formula (I)

Wherein R is selected from the group consisting of hydrogen, COOH, CN, optionally substituted C ₁ -C ₁₀ alkyl, optionally substituted C ₂ -C ₁₀ alkenyl, optionally substituted C ₂ -C ₁₀ alkynyl, Optionally substituted C ₃ -C ₁₀ cycloalkyl, optionally substituted C ₆ -C ₁₀ aryl or 5-10 member optionally substituted heteroaryl, wherein the alkyl is optionally substituted The base is selected from the group consisting of halogen, hydroxyl, amine and C ₁ -C ₄ alkoxy, and the substituents of other groups optionally present are selected from the group consisting of halogen, hydroxyl, amine, C ₁ -C ₄ alkyl and C ₁ -C ₄ alkoxy; and - at least one selected from the group consisting of nonionic, anionic, cationic and amphoteric polymers and having at least 500 mPa. s, preferably 1,000 mPa. s, more preferably 1,500mPa. s and more preferably 2,000 mPa. The viscosity of s (a known thickener by a Brookfield viscometer measured at 20 ° C with a polymer concentration of 1% by weight in water at 10 rpm for 1 minute).

The composition may be formulated as a one-part composition, or as a two-part composition comprising portions A and B, separately storing portions A and B and mixing them prior to application to the hair, wherein portion A comprises a carboxy group of formula (I) The acid and part B comprise at least one of a fragrance, a surfactant or a conditioning component, and wherein the polymeric thickener is included in either or both of Part A and Part B. Improved fragrance stability was observed for the two-part composition.

In another aspect, the invention provides a method for semi-permanent hair straightening comprising the steps of: (a) applying a hair straightening composition to the hair, the composition being as above a defined one-part composition or a two-part composition as a mixture of parts A and B; (b) leaving the composition on the hair for 1 to 120 minutes; (c) rinsing the hair as appropriate; (d) drying the hair (e) treating the hair by a hair iron having a surface temperature of 180 ± 50 ° C; (f) Rinse and/or wash with shampoo and dry as appropriate.

Other aspects of the invention relate to the use of the composition for straightening hair and a kit for straightening hair, comprising a straightening composition and a straightening iron.

The hair straightening composition according to the present invention may satisfy one of the following requirements (1), (2) or (1) + (2): (1) The hair straightening composition does not contain two C in the molecule ₅ -C ₂₄ linear or branched, saturated or unsaturated hydrocarbon group of quaternary ammonium salts, such hydrocarbon groups may be the same or different and are optionally substituted with one or more substituents selected from halo, hydroxy, amino and C ₁ -C ₄ Substituted by a substituent of an alkoxy group; (2) The hair straightening composition does not have 13.0 wt.% glyoxylic acid monohydrate (corresponding to 10.4 wt.% glyoxylic acid) and 1.6 wt.% dehydrogenase And an aqueous solution having a pH of 1.5 (adjusted by NaOH).

It has recently been discovered that carboxylic acids of formula (I) such as glyoxylic acid provide significant semi-permanent straightening effects. However, there is a problem that excessive smoke generation occurs when the hair is treated with a straightening iron at a high temperature after application of the acid. This problem has not been resolved in the prior art.

The inventors have discovered that this problem can be solved by combining the carboxylic acid of formula (I) with a specific polymeric thickening agent which also provides improved hair feel during application.

1. Carboxylic acid of formula (I)

The straightening composition comprises at least one carboxylic acid of the following formula (I) as an active component for achieving a straightening effect: R-CO-COOH formula (I)

Wherein R is selected from the group consisting of hydrogen, COOH, CN, optionally substituted C ₁ -C ₁₀ alkyl, optionally substituted C ₂ -C ₁₀ alkenyl, optionally substituted C ₂ -C ₁₀ alkynyl, Optionally substituted C ₃ -C ₁₀ cycloalkyl, optionally substituted C ₆ -C ₁₀ aryl or 5-10 member optionally substituted heteroaryl, wherein the alkyl is optionally substituted The base is selected from the group consisting of halogen, hydroxyl, amine and C ₁ -C ₄ alkoxy, and the substituents of other groups optionally present are selected from the group consisting of halogen, hydroxyl, amine, C ₁ -C ₄ alkyl and C ₁ -C ₄ alkoxy.

As preferred examples, glyoxylic acid, pyruvic acid and 2-ketobutyric acid can be mentioned.

The carboxylic acid of formula (I) can be included in the composition in its free acid form. The carbonyl group adjacent to the acid group of the acid may also be present in a hydrated form. In addition to the free acid form and its hydrate, a salt of an acid or a hydrate can also be used.

A hydrate of the acid of formula (I) can be formed when the composition is provided in an aqueous medium. For example, glyoxylic acid (H-CO-COOH) in an aqueous solution is quantitatively present in the form of a hydrate (HC(OH) ₂ -COOH). In addition, the hydrate can also be condensed into a dimer.

Salts of the carboxylic acids of formula (I) can also be used. As an example, an alkali metal salt such as a sodium salt or a potassium salt; an alkaline earth metal salt such as a magnesium salt or a calcium salt; and tertiary and quaternary ammonium salts can be mentioned.

In the present invention, glyoxylic acid, a salt thereof and a hydrated form thereof are more preferred carboxylic acids of the formula (I).

The concentration of the at least one carboxylic acid of the formula (I) and/or its hydrate and/or its salt is from 0.1 to 40% by weight, preferably from 0.5 to 40% by weight, based on the total weight of the straightening composition, more preferably From 2.5 to 40% by weight, more preferably from 0.5 to 30% by weight, still more preferably from 1 to 25% by weight and still more preferably from 2.5 to 20% by weight, and more preferably from 2.5 to 14% by weight.

As noted above, conventional permanent hair shaping/straightening techniques are based on the reorganization of disulfide bridges and involve breaking the disulfide bond by using a sulfur-based reducing agent or alkaline agent, followed by shaping the hair and forming a new bond. (ie, a disulfide bond formed by the action of an oxidizing agent or a thioether bond, respectively). Compared to such permanent straightening methods, the present invention does not utilize the breaking of disulfide bonds and the fixation of newly shaped bonds. Thus, the straightening compositions of the present invention do not require the presence of a sulfur-based reducing agent, and preferably do not contain a sulfur-based reducing agent. However, up to 2% by weight, based on the total composition, of the sulfur-based reducing agent does not interfere with the straightening performance of the composition. Thus, the composition typically has less than 2% by weight of a sulfur-based reducing agent, and preferably is free of sulfur-based Original agent.

2. Thickening polymer

The straightening composition comprises at least one polymeric thickener selected from the group consisting of nonionic, anionic, cationic and amphoteric polymers having a thickness of at least 500 mPa. The viscosity of s is determined by a Brookfield viscometer using a suitable shaft at a polymer concentration of 1% by weight in water and at 20 ° C, for example at 10 rpm for 1 minute.

The total concentration of the one or more thickeners is usually from 0.01 to 15 wt.%, preferably from 0.05 to 10 wt.%, more preferably from 0.1 to 5 wt.%, and still more preferably from 0.5 to 2 wt%, based on the weight of the straightening composition. Within .%.

Nonionic polymer

Any cosmetically acceptable nonionic thickening polymer commonly used in the field of hair cosmetic compositions can be used as the polymeric thickener in the compositions of the present invention. The composition may comprise a single or multiple nonionic polymers, and may further comprise one or more anionic, cationic and/or amphoteric polymers in combination with the nonionic polymer.

Examples of nonionic polymers include neutral polysaccharides and derivatives thereof, such as ethers or esters. In this connection, mention may be made of neutral gums such as guar gum, hydroxypropyl guar; cellulose ethers such as hydroxyethyl cellulose (HEC), methyl hydroxyethyl cellulose (MHEC), ethyl Hydroxyethyl cellulose (EHEC), methyl ethyl hydroxyethyl cellulose (MEHEC), hydroxypropyl cellulose (HPC), hydroxypropyl methyl cellulose (HPMC); hydrophobic modified derivatives thereof, Such as HM-EHEC, starch and dextrin.

Cellulose ethers such as MHEC or MEHEC are preferred. As a commercially available example, mention may be made of STRUCTURE® CEL 12000 M (MEHEC) (available from AkzoNobel, digital indicating viscosity, cps).

Anionic polymer

Any cosmetically acceptable anionic thickening polymer commonly used in the field of hair cosmetic compositions can be used as the polymeric thickener in the compositions of the present invention. The composition can be packaged Single or multiple anionic polymers are included, and may further comprise one or more nonionic, cationic and/or amphoteric polymers in combination with the anionic polymer.

Examples of anionic polymers include anionic polysaccharides and derivatives thereof, such as alginate, pectin, hyaluronic acid; anionic gums such as Sanxian gum, dehydrogenosin, hydroxypropyl trisin, gum arabic, carrageen Gum or tragacanth; or an anionic cellulose derivative such as carboxymethyl cellulose (CMC).

Other examples include synthetic anionic polymers such as polyacrylic acid or copolymers containing acrylic acid and neutral ethylene and/or acrylic monomers, and salts thereof, such as sodium polyacrylate.

Considering the stability of pH, Sanxianjiao, hydroxypropyltrisin and dehydrogenosin are especially preferred.

Cationic polymer

Any cosmetically acceptable cationic thickening polymer commonly used in the field of hair cosmetic compositions can be used as the polymeric thickener in the compositions of the present invention. The composition may comprise a single or multiple cationic polymers, and may further comprise one or more nonionic, anionic and/or amphoteric polymers in combination with a cationic polymer.

The cationic polymer is a polymer having a cationic group such as a quaternary ammonium or a group capable of ionizing into a cationic group such as a primary, secondary or tertiary amine group. The cationic polymer is usually a polymer containing an amine group or an ammonium group in a side chain of a polymer chain, or a polymer including a diallyl quaternary ammonium salt as a constituent unit.

Among the cationic polymers, polymers having a tertiary or tertiary ammonium group are preferred, and polymers having a quaternary ammonium group are preferred because such polymers are not readily compatible with the carboxylic acid of formula (I). Carbonyl condensation. In contrast, polymers having a primary amine group are less preferred because such polymers may undergo a condensation reaction with a carboxylic acid of formula (I) and thus reduce their effective concentration.

Examples of preferred cationic polymers include cationized cellulose, cationic starch, cationic guar, ethylene or (meth)acrylic polymer having a quaternary ammonium side chain or copolymerization , (meth) acrylate / methacrylate copolymer, amine substituted polyacrylate crosspolymer, polymer or copolymer of diallyl quaternary ammonium salt and quaternized ammonium polyvinylpyrrolidone .

As an example of an ethylene or (meth)acrylic polymer or copolymer having a quaternary ammonium side chain, mention may be made of poly(2-methylpropenyloxyethyltrimethylammonium chloride) (poly quaternary Ammonium-37).

Specific examples of the quaternized ammonium polyvinylpyrrolidone include a quaternary ammonium salt synthesized from a copolymer of vinylpyrrolidone (VP) and dimethylaminoethyl methacrylate and diethyl sulfate (poly quaternary Ammonium-11).

As an example of the (meth) acrylate/amino acrylate copolymer, an acrylate/amino acrylate/C10-30 alkyl PEG-20 itaconate copolymer can be mentioned.

As an example of the amine-substituted polyacrylate crosslinked polymer, a polyacrylate-1 crosslinked polymer can be mentioned.

Specific examples of the cationized cellulose include a quaternary ammonium salt polymer (polytetra-ammonium-10) obtained by adding glycidyl trimethylammonium chloride to hydroxyethyl cellulose, and a hydroxyethyl group. Cellulose/dimethyldiallylammonium chloride copolymer (polytetramine-4), and epoxide substituted with hydroxyethyl cellulose and trimethylammonium and glutamate substituted with lauryl dimethyl ammonium A polymeric quaternary ammonium salt (polytetra-ammonium-67) formed by the reaction of an oxide.

In these examples, polytetraamethylene-37 is especially preferred.

Amphoteric polymer

Amphoteric polymers contain both cationic and anionic groups. From a structural point of view, the amphoteric polymer can be derived from any of the cationic polymer types by additionally introducing an anionic group or a co-monomer.

Like cationic polymers, amphoteric polymers can also provide hair conditioning benefits, specifically in the case of positive net charges.

Any cosmetically acceptable two commonly used in the field of hair cosmetic compositions The thickening polymer can be used as a polymeric thickener in the compositions of the present invention. The composition may comprise a single or multiple amphoteric polymers and may further comprise one or more nonionic, anionic and/or cationic polymers in combination with the amphoteric polymer.

As examples of amphoteric polymers, mention may be made of carboxy-modified or sulfonate-modified cationic polysaccharides such as carboxymethyl polyglucamine.

Other examples include cationic ethylene or copolymers of (meth)acrylic monomers with (meth)acrylic acid, such as dimethyldiallyl ammonium chloride/acrylic acid copolymer (polytetraamethylene-22).

As the amphoteric polymer, polytetraamethylene-22 is particularly preferred.

3. Surfactant

The straightening composition can comprise a surfactant. As the surfactant, any of a cationic surfactant, a nonionic surfactant, an amphoteric surfactant, and an anionic surfactant can be used. It is also possible to use two or more types of surfactants in a combined form.

The cationic surfactant is preferably a single long chain alkyl quaternary ammonium salt having one C ₈ -C ₂₄ alkyl residue and three C ₁ -C ₄ alkyl residues.

Preferably, the at least one monoalkyl quaternary ammonium surfactant is selected from the group consisting of compounds of the formula:

Wherein R ₈ is a saturated or unsaturated, branched or linear alkyl chain having 8 to 22 C atoms or R ₁₂ -CO-NH-(CH ₂ ) _n -

Wherein R ₁₂ is a saturated or unsaturated, branched or linear alkyl chain having 7 to 21 C atoms and n is an integer from 1 to 4, or R ₁₂ -CO-O-(CH ₂ ) _n -

Wherein R ₁₂ is a saturated or unsaturated, branched or linear alkyl chain having 7 to 21 C atoms and n is an integer of from 1 to 4, and R ₉ , R ₁₀ and R ₁₁ are independently from each other having 1 to An alkyl group of 4 carbon atoms, a hydroxyalkyl chain having 1 to 4 carbon atoms or an ethoxy or propoxy group having a number of ethoxy or propoxy groups ranging from 1 to 4, and X is a chloride ion , bromide, methyl sulfate or ethyl sulfate.

Suitable cationic surfactants are, for example, long chain quaternary ammonium compounds which can be used singly or in admixture with each other, such as cetyltrimethylammonium chloride, myristyltrimethylammonium chloride, behenyl sulphate Ammonium chloride, trimethyl cetyl ammonium bromide, stearyl trimethyl ammonium chloride, stearyl trimethyl ammonium chloride and stearyl ammonium trimethyl ammonium chloride.

Examples of the nonionic surfactant include polyoxy-C _1-4 alkylene C _8-24 alkyl ether, polyoxy-C _1-4 alkylene C _8-24 alkylene alkenyl ether, advanced (C ₁₂ -C ₂₄ ) fatty acid sucrose ester, polyglycerol C _8-24 fatty acid ester, advanced (C ₁₂ -C ₂₄ ) fatty acid mono or diethanol decylamine, polyoxyethylene hardened castor oil, polyoxyethylene sorbitan C _8-24 fatty acid ester, polyoxyethylene sorbitol C _8-24 fatty acid ester, C _8-24 alkyl saccharide surfactant, C _8-24 alkyl amine oxide and C _8-24 alkyl guanamine Amine oxide.

Examples of amphoteric surfactants include imidazoline-based surfactants, carbonylbetaine-based surfactants, guanylamine-based betaine-based surfactants, sulfobetaine-based surfactants, hydroxysulfobeta-based surfactants. a surfactant for alkali and a surfactant based on decyl sulfobetaine.

Examples of anionic surfactants include alkylbenzene sulfonates, alkyl or alkenyl ether sulfates, alkyl or alkenyl sulfates, olefin sulfonates, alkane sulfonates, saturated or unsaturated fatty acid salts, alkyl groups Or an alkenyl ether carboxylate, an α-sulfonate fatty acid salt, an N-guanidino acid type surfactant, a phosphoric acid monoester or diester type surfactant, and a sulfosuccinate. Examples of alkyl ether sulfates include polyoxyethylene alkyl ether sulfates. Examples of the relative ions of the anionic residues of such surfactants include alkali metal ions such as sodium ions or potassium ions; Alkaline earth metal ion of calcium ion or magnesium ion; ammonium ion; and alkanolamine having 1 to 3 alkanol groups (each having 2 or 3 carbon atoms) (for example, monoethanolamine, diethanolamine, triethanolamine or triiso) Propanolamine).

The surfactant may be used singly or in combination of two or more kinds. When the surfactant is added to the straightening composition, the surfactant is usually present in an amount of from 0.05 to 10% by weight, more preferably from 0.1 to 5% by weight, based on the total weight of the straightening composition.

4. Conditioning components

The straightening composition can optionally comprise conditioning components suitable for application to the hair. The conditioning component is typically an oil or other polymer that adheres to the hair and improves hand and combability.

When the conditioning component is used, its total content is preferably from 0.01 to 30% by weight, more preferably from 0.05 to 20% by weight, and still more preferably from 0.1% to 10% by weight, based on the total weight of the straightening composition.

Examples of conditioning components typically include polyoxo, higher alcohols and organic conditioning oils (e.g., hydrocarbon oils, polyolefins, and fatty acid esters), as well as cationic surfactants and cationic or amphoteric polymers, including those described above.

The composition may comprise a single type of conditioning component, or a combination of two or more.

Polyoxyl

In order to improve the feeling of use, the straightening composition preferably contains polyfluorene oxide. Examples of polyoxymethylene include dimethyl polyoxyalkylene and modified polyfluorene oxide (for example, amine-modified polyfluorene oxide, fluorine-modified polyfluorene oxide, alcohol-modified polyoxyl Polyether modified by polyether, polyoxyl modified by epoxy group, polyoxazoline polyoxyl (as described in JP A 2-276824) or alkyl modified polyoxyl However, dimethyl polyoxyalkylene, polyether modified polyfluorene oxide and amine modified polyoxyl oxide are preferred.

The dimethyl polyoxane may be any cyclic or acyclic dimethyl siloxane polymer, and examples thereof include SH200 series, BY22-019, BY22-020, BY11-026, B22-029, BY22- 034, BY22-050A, BY22-055, BY22-060, BY22-083, FZ-4188 (all from Dow Corning Toray Co., Ltd.), KF-9008, KM-900 series, MK-15H and MK-88 (all from Shin-Etsu Chemical Co., Ltd.).

The polyether-modified polyfluorene oxide may be any polyoxyalkylene having a polyoxyalkylene group, and the group constituting the polyoxyalkylene group may be an oxyethyl group or an oxypropyl group. More specific examples include KF-6015, KF-945A, KF-6005, KF-6009, KF-6013, KF-6019, KF-6029, KF-6017, KF-6043, KF-353A, KF-354A, KF -355A (all from Shin-Etsu Chemical Co., Ltd.), FZ-2404, SS-2805, FZ-2411, FZ-2412, SH3771M, SH3772M, SH3773M, SH3775M, SH3749, SS-280X series, BY22-008 M, BY 11-030 and BY 25-337 (all from Dow Corning Toray Co., Ltd.).

The amine-modified polyfluorene oxide may be any polyfluorene oxide having an amine group or an ammonium group, and examples thereof include an amine group-modified polycondensate in which all or a part of terminal hydroxyl groups are terminated by a methyl group or the like. Oxygen oil, and amine-terminated dimethyl polyoxane without a blocked end. A preferred example of the amino group-modified polyfluorene oxide may be a compound represented by the following formula:

Wherein R' represents a hydroxyl group, a hydrogen atom or R ^X ; R ^X represents a substituted or unsubstituted monovalent hydrocarbon group having 1 to 20 carbon atoms; and D represents R ^X , R"-(NHCH ₂ CH ₂ ) _m NH ₂ , OR ^X or a hydroxyl group; R" represents a divalent hydrocarbon group having 1 to 8 carbon atoms; m represents the number of 0 to 3; p and q represent a number which is a total of the number average form equal to or greater than 10 and less than 20,000 Preferably, it is equal to or greater than 20 and less than 3000, more preferably equal to or greater than 30 and less than 1000, and still more preferably equal to or greater than 40 and less than 800.

Specific examples of suitable commercially available products of amine-modified polyfluorene include amine-modified polyoxyxides such as SF8452C, SS-3551 (all from Dow Corning) Toray Co., Ltd.), KF-8004, KF-867S and KF-8015 (all from Shin-Etsu Chemical Co., Ltd.); and an amine-terminated dimethyl polyoxane emulsion such as SM8704C, SM8904, BY22-079, FZ-4671, and FZ-4672 (all from Dow Corning Toray Co., Ltd.).

The total content of such polyfluorene oxides in the straightening composition of the present invention is usually from 0.1 to 20% by weight, preferably from 0.2% to 10% by weight and more preferably from 0.5 to the total weight of the straightening composition. 5wt.%.

Oil component

To improve the feel of use, the straightening composition may also include an organic conditioning oil. The organic conditioning oil which is preferably used as the conditioning component is preferably a low viscosity and water insoluble liquid, and is selected from the group consisting of hydrocarbon oils having at least 10 carbon atoms, polyolefins, fatty acid esters, fatty acid decylamines, and polyalkylenes. Alcohols and mixtures thereof. The viscosity of the organic conditioning oil is preferably 1 to 200 mPa as measured at 40 ° C. s, more preferably 1 to 100 mPa. s, and more preferably 2 to 50 mPa. s. For the determination of viscosity, a capillary viscometer can be used.

Examples of the hydrocarbon oil include a cyclic hydrocarbon, a linear aliphatic hydrocarbon (saturated or unsaturated), and a branched aliphatic hydrocarbon (saturated or unsaturated), and also include a polymer or a mixture thereof. The linear hydrocarbon oil preferably has from 12 to 19 carbon atoms. Branched chain hydrocarbon oils include hydrocarbon polymers, and preferably have more than 19 carbon atoms.

The polyolefin is a liquid polyolefin, more preferably a liquid poly-?-olefin, and more preferably a hydrogenated liquid poly-?-olefin. The polyolefin used herein is prepared by polymerizing an olefin monomer having 4 to 14 carbon atoms, and preferably 6 to 12 carbon atoms.

The fatty acid ester can be, for example, a fatty acid ester having at least 10 carbon atoms. Examples of such fatty acid esters include esters having a hydrocarbon chain derived from a fatty acid and an alcohol (for example, a monoester, a polyol ester or a di- and tricarboxylic acid ester). The hydrocarbyl group of such fatty acid esters may have another compatible functional group such as a decylamino group or an alkoxy group as a substituent, or the hydrocarbyl group may be covalently bonded to these functional groups. More specifically, it is preferred to use a fat having a fatty acid chain of 10 to 22 carbon atoms. An alkyl and alkenyl ester of an acid, a carboxylic acid ester of an aliphatic alcohol having an aliphatic chain derived from an alkyl group having 10 to 22 carbon atoms and/or an alkenyl alcohol, and mixtures thereof. Specific examples of such preferred fatty acid esters include isopropyl isostearate, hexyl laurate, isohexyl laurate, isohexyl palmitate, isopropyl palmitate, isopropyl myristate, oleic acid Oxime ester, isodecyl oleate, cetyl stearate, decyl stearate, dihexadecyl adipate, lauryl lactate, myristyl lactate, cetyl lactate, stearic acid Acid oleyl alcohol ester, oleic acid oleyl alcohol ester, oleic acid oleic acid ester, lauryl acetate, cetyl propionate and dioleyl adipate.

Other suitable oil components are natural oils such as paraffin oil and natural triglycerides.

Suitable natural triglycerides are argan oil, shea oil, karite oil, olive oil, almond oil, avocado oil, castor oil, coconut oil, palm oil, sesame oil, peanut oil , sunflower oil, peach oil, wheat germ oil, macadamia nut oil, Australian walnut oil, night primrose oil, jojoba oil, castor oil, soybean oil, lanolin, passion fruit essence oil, black cumin oil, colored glass Oil, grape seed oil, hemp seed oil, Hawaiian stone fruit oil and rosehip oil.

The organic conditioning oil may be used in combination of two or more kinds, and the total concentration is usually 0.1 to 20 wt.%, preferably 0.2 to 10 wt.%, more preferably 0.5 to the total weight of the straightening composition. Within 5wt.% range.

Alcohol

The straightening composition may also contain a higher alcohol having 8 carbon atoms or more from the viewpoint of improved touch and stability. Generally, the higher alcohol has from 8 to 22 carbon atoms, and preferably from 16 to 22 carbon atoms. Specific examples thereof include cetyl alcohol, stearyl alcohol, behenyl alcohol, and mixtures thereof.

The higher alcohol may be used in combination of two or more kinds, and the content thereof is usually from 0.1 to 20% by weight, preferably from 0.2 to 10% by weight, more preferably from 0.5 to 5% by weight based on the total weight of the straightening composition. .%.

Further, a polyol may be suitably included in the composition. Example package of polyalkylene glycol Polyethylene glycol and polypropylene glycol are used, and a mixture of the two may be used, or a copolymer of ethylene oxide and propylene oxide may also be used.

5. Straightening composition of the composition

The straightening composition of the present invention may suitably be in the form of a thickened solution or gel, emulsion, cream, paste and mousse.

The total viscosity of the composition generally depends on the type and amount of polymeric thickener and is measured by a Brookfield viscometer at 20 ° C using a suitable shaft, such as at 10 rpm for 1 minute, usually It is at least 1000mPa*s. If the composition is provided in the form of a thickened solution, gel or emulsion, the viscosity is usually in the range of 1,000 to 25,000, preferably 2,500 to 15,000 mPa*s.

In order to provide sufficient straightening effect, as measured directly and at ambient temperature (25 ° C), the pH of the straightening composition is 4.0 or less, preferably in the range of 1 to 3.5, more preferably 1 to 3 and more preferably 1.5 to 3. The pH of the composition can be adjusted using a known alkaline solution, preferably with a sodium hydroxide solution.

Gel formulation

A preferred straightening composition can be formulated in a gel form comprising the following ingredients:

(Gel formulation 1)

Weight%

2 to 20 glyoxylic acid;

0.1 to 2 anionic thickening polymer, preferably trisin or hydroxypropyl trisin or dehydrogenose;

0.1 to 1 surfactant, such as cocoamidopropyl betaine or cocobetaine, decyl glucoside, sodium lauryl ether sulfate

Alternative preferred gel formulations are described below.

(Gel formulation 2)

Weight%

2 to 20 glyoxylic acid;

0.1 to 2 nonionic thickening polymer, preferably MHEC or MEHEC;

0.1 to 1 surfactant, such as cocoamidopropyl betaine or cocobetaine, decyl glucoside, sodium lauryl ether sulfate or cetyltrimethylammonium chloride

(Gel formulation 3)

Weight%

2 to 20 glyoxylic acid;

0.1 to 2 cationic thickening polymer, preferably polytetraamethylene-37;

0.1 to 1 surfactant, such as cocoamidopropyl betaine or cocobetaine, decyl glucoside or cetyltrimethylammonium chloride

(Gel formulation 4)

Weight%

2 to 20 glyoxylic acid;

0.1 to 2 amphoteric thickening polymer, preferably polytetraamethylene-22;

0.1 to 1 surfactant, such as cocoamidopropyl betaine or cocobetaine, decyl glucoside, sodium lauryl ether sulfate or cetyltrimethylammonium chloride

Gel formulations 1-4 may optionally contain other ingredients such as surfactants and/or conditioning components. Cosmetically acceptable additives such as preservatives, dyes and fragrances may be added as needed. The rest is water. The pH of the gel formulation 1-4 can be adjusted to 1.5 to 2.5 using a base such as sodium hydroxide as necessary.

The viscosity of the gel formulations 1-4 depends on the type and amount of thickening polymer and is measured by a Brookfield viscometer at 20 ° C using a suitable shaft, for example at 10 rpm for 1 minute. It is usually in the range of 1,000 to 25,000, preferably 2,500 to 15,000 mPa*s.

Emulsion

To further enhance ease of use, it is also possible to formulate the straightening composition in the form of an emulsion. Preferred emulsions comprise the same amount of the same ingredients as the gel formulations 1-4 described above, and additionally include fatty alcohols, optionally surfactants which are preferably cationic surfactants and/or preferably A gel emulsion of a combination of polyoxo oil components. The preferred emulsion formulation is described below.

(emulsion formulation 1)

2 to 20 wt.% glyoxylic acid;

0.1 to 2 wt.% anionic thickening polymer, preferably trisin, hydroxypropyl trisin or dehydrogenose;

1-5 wt.% fatty alcohol, preferably cetearyl alcohol

1-5 wt.% C _12-24 alkyl trimethylammonium salt, such as behenyl trimethyl ammonium chloride

Emulsion formulation 1 may optionally include other ingredients such as surfactants and/or conditioning components. Cosmetically acceptable additives such as preservatives, dyes and fragrances may be added as needed. The rest is water. The pH of the Emulsion Formulation 1 can be adjusted to 1.5 to 2.5, if necessary, using a base such as sodium hydroxide.

Two-component formulation

In the case where it is desired to include a compound containing an ester moiety or other acid-sensitive group such as a fragrance or a surfactant and/or a conditioning component, there is a possibility that the storage stability at the above pH value is lowered. Further, the aromatic compound may also react undesirably with the carbonyl group of the carboxylic acid of the formula (I), which lowers the storage stability.

To avoid such problems, it may be preferred in these situations to formulate the straightening composition in the form of a two-part system comprising portions A and B, separately storing portions A and B and mixing them prior to application to the hair.

Part A comprises a carboxylic acid of formula (I) and part B comprises at least one of a fragrance, a surfactant and a conditioning agent. Add thickener and acid-insensitive interface as appropriate The agent and the conditioning agent are in Part A, Part B or both parts.

For fragrances, use Common Fragrance and Flavor Materials: Preparation, Properties and Uses (John Wiley & Sons, 5th edition, 2006), Perfume and Flavor Chemicals, Volumes 1 and 2 of Horst Surburg, Johannes Panten. The fragrance material (published by the author in 1969), Steffen Arctander, Perfume and Flavor Materials of Natural Origin (published by the author in 1961).

From the standpoint of stability, the fragrance is preferably orange, more preferably one or more selected from the group consisting of limonene, decene, citral, dihydromyrcenol, 2-methyl-4-phenyl-1- An orange-flavored fragrance raw material of pentamfleur, lemon oil, orange oil, citrus oil and lime oil. The content of the aromatic-flavoring raw material is preferably from 5 to 100%, more preferably from 20 to 90%, still more preferably from 30 to 80%.

From the viewpoint of the same reason, the portion A preferably comprises an aromatic agent having an orange flavor, more preferably one or more selected from the group consisting of limonene, decene, citral, dihydromyrcenol, 2-methyl-4-benzene. An orange-flavored fragrance raw material for keto-1-pentanol, lemon oil, orange oil, citrus oil, and lime oil.

The pH of Part B is adjusted such that the ingredients have sufficient storage stability, typically in excess of 4 and typically in the range of 4 to 8, while Part A has a pH of less than 4, typically in the range of 1 to 3.5. The final pH after mixing portions A and B is 4 or lower, preferably 1 to 3.5.

Preferred two component formulations are described below.

Two-component formulation 1 (gel)

Part A: Gel component containing glyoxylic acid

5-40 wt.% glyoxylic acid;

0.2 to 4 wt.% anionic thickening polymer, preferably trisin, dehydrogenosene or hydroxypropyl trisin

Acid-insensitive components may be added as needed. The rest is water, and if necessary, The pH of the base such as NaOH is adjusted to pH 1-3, preferably 1.5 to 2.

Part B: Conditioning component comprising an ester compound and/or a fragrance

1-4 wt.% fatty acid ester, preferably isopropyl palmitate or isopropyl myristate

2-8% PEG-40 hydrogenated castor oil

0-2% fragrance

Other ingredients such as surfactants or other conditioning components may be added as needed. The rest is water. The pH is 6-7.

Portions A and B are stored separately and mixed prior to use at a predefined ratio such as 1:1.

Two-component formulation 2 (gel-emulsion)

Part A: Gel component containing glyoxylic acid

5-40 wt.% glyoxylic acid;

0.2 to 4 wt.% anionic thickening polymer, preferably Sanxian gum or dehydrogenase or hydroxypropyl trisin

Acid-insensitive components may be added as needed. The balance is water, and if necessary, the pH can be adjusted to pH 1-3, preferably 1.5 to 2, by a base such as NaOH.

Part B: Conditioning component in the form of an emulsion comprising an ester compound and/or a fragrance

1-8 wt.% fatty alcohol, preferably cetearyl alcohol

1-8wt.% polyoxylized oil

1-8 wt.% C _12-24 alkyl trimethylammonium salt, such as behenyl trimethyl ammonium chloride

0.5-4 wt.% fatty acid ester, preferably isopropyl palmitate or isopropyl myristate

0-2% fragrance

Other ingredients such as surfactants or other conditioning components may be added as needed. The rest is water. The pH is 6-7.

Portions A and B are stored separately and mixed prior to use at a predefined ratio such as 1:1.

6. Hair treatment method

The hair treatment method of the present invention utilizes an acid of formula (I) such as glyoxylic acid as the active agent to achieve semi-permanent straightening of the hair. The straightening effect of this method is not achieved by breaking the disulfide bond by the action of reduction or strong base. Therefore, it is not necessary to use a reducing composition or an alkali relaxant (lanine thiamine).

In step (a) of the method of the invention, the straightening composition is applied to the hair. The application weight ratio of hair to composition is from 0.5:2 to 2:0.5, preferably from 0.5:1 to 1:0.5, more preferably about 1:1.

After application, the straightening composition is allowed to remain on the hair at a temperature of 45 ° C or lower, preferably at ambient temperature for from 1 to 120 minutes, preferably from 5 to 90 minutes, more preferably from 10 to 60 minutes. More preferably, it is 15 to 45 minutes (step (b)). Subsequently, the straightening composition is rinsed off from the hair as appropriate (step (c)).

In a subsequent step (d), the hair is dried to avoid excessive steam generation in subsequent steps of treating the hair by the hair iron. Usually, a hair dryer is used for this purpose. The hair is preferably dried under continuous combing to prevent tangling of the hair. After drying, the hair is treated with a hair iron having a surface temperature of 180 ± 50 ° C, preferably 170 to 200 ° C. A commonly used straightening iron can be used for this purpose (step (e)). Finally, the water may optionally be rinsed with water and/or shampooed and dried again (step (f)).

Instance

The invention will now be illustrated by the following non-limiting examples.

Reference example

A straightening composition in the form of an emulsion is prepared by mixing the following ingredients:

Example 1

A straightening composition in the form of a gel is prepared by mixing the following ingredients:

Example 2

A straightening composition in the form of a gelled emulsion is prepared by mixing the following ingredients:

Test case 1

A bundle of about 2 g of hair was washed by a commercially available shampoo and blown dry. Subsequently, it was treated with about 1 g of the straightening composition, kept at room temperature for about 15 minutes and dried with a hair dryer. Subsequently, the hair tresses were treated 6 times with a flat hair iron having a surface temperature of 220 °C. The generation of smoke on the surface of the hair and the sliding of the hair iron were observed during perm. The coated/uncoated feel of the tress is then visually and/or subjectively assessed by the hair stylist.

The efficacy of the reference examples of the present invention and the compositions of Examples 1 and 2 were evaluated with respect to smoke generation and ease of use/feeling. The results are shown in Table 1 below.

As is apparent from the results, the compositions according to Examples 1 and 2 of the present invention provide a substantial reduction in smoke generation during perm and are also advantageous in view of the hair feel during application. The emulsion formulations of the Reference Example and Example 2 facilitate the sliding of the hair iron compared to the conventional gel formulation of Example 1. In Example 2, the slip was significantly improved.

Example 3: Two-component gel-emulsion

Part A: Gel component (pH 1.5)

Part B: Emulsion component (pH 6.5)

Five variants of Part B (without fragrance, Fragrance A-D) differing in terms of fragrance were prepared.

* Fragrance A-D: See the table below.

The portions A and B were mixed at a ratio of 1:1 to produce a mixed gel-emulsion composition having a pH of 1.6 to 1.7.

Test case 2

The storage stability of Part A and B and the mixed gel emulsion of Example 3 was evaluated by comparing the odor of a fresh mixture, a mixture stored at 50 ° C for one month, and a mixture of components stored at 50 ° C for one month. Several variants of Part B were tested which differed in terms of the fragrance component. Fragrance assessment is performed by a trained team of technicians. The following results were obtained as in Table 2.

Example 4: Two-component gel system

Part A: Gel component (pH 1.5)

Part B: Conditioning component containing ester (pH 5-7)

Two variants of Part B were prepared comprising isopropyl palmitate and isopropyl myristate as ester components, respectively.

The portions A and B were mixed at a ratio of 1:1 to produce a mixed gel composition having a pH of 1.6 to 1.7.

Test example 3

The effect on the storage stability of the fresh mixture of parts A and B of Example 4 or the mixture aged at 40 ° C for three days was evaluated by comparing the hair characteristics and the curling of the hair for natural hair and bleached hair. The hair tresses were treated in the same manner as described above for Test Example 1, and then rinsed and dried. The following results as presented in Table 3 were obtained.

Example 5

The pH of this example is 1.8.

Example 6

Example 7

Example 8

Example 9

Example 10

Water to 100

Example 11

Claims (25)

A hair straightening composition having a pH of 4 or less and comprising: at least one carboxylic acid of formula (I) having a total concentration in the range of from 0.1 to 40% by weight, based on the weight of the entire composition, and/or a hydrate thereof and/or a salt thereof: R-CO-COOH wherein R is selected from the group consisting of hydrogen, COOH, CN, optionally substituted C ₁ -C ₁₀ alkyl, optionally substituted C ₂ - C ₁₀ alkenyl, optionally substituted C ₂ -C ₁₀ alkynyl, optionally substituted C ₃ -C ₁₀ cycloalkyl, optionally substituted C ₆ -C ₁₀ aryl or 5-10 member a substituted heteroaryl group wherein the alkyl group is optionally selected from the group consisting of halogen, hydroxy, amine and C ₁ -C ₄ alkoxy, and such other groups are optionally substituted The base is selected from the group consisting of halogen, hydroxyl, amine, C ₁ -C ₄ alkyl and C ₁ -C ₄ alkoxy; and at least one polymeric thickener selected from the group consisting of nonionic, anionic, cationic and amphoteric polymers, The polymeric thickener has a Brookfield viscometer measured at a polymer concentration of 1% by weight in water and at 20 ° C measured at least 500 mPa. s viscosity. The hair straightening composition of claim 1 which is a two-part composition comprising portions A and B, the portion A and the portion B are provided for separate storage and mixed prior to application to the hair, wherein part A comprises formula (I The carboxylic acid and part B comprise at least one of a fragrance, a surfactant or a conditioning component, and wherein the polymeric thickener is included in either or both of Part A and Part B. The hair straightening composition of claim 2, wherein the fragrance is one or more selected from the group consisting of limonene, decene, citral, dihydromyrcenol, 2-methyl-4-phenyl-1-pentanol, A lemon-flavored fragrance material for lemon oil, orange oil, citrus oil and lime oil. A hair straightening composition according to any one of claims 1 to 3, wherein the carboxylic acid of the formula (I) It is glyoxylic acid and/or its hydrate and/or its salt. The hair straightening composition according to any one of claims 1 to 4, which comprises the at least one carboxylic acid of the formula (I) in a total concentration of from 0.5 to 40% by weight based on the total weight of the composition. Or a hydrate thereof and/or a salt thereof. A hair straightening composition according to claim 5, which comprises the at least one carboxylic acid of the formula (I) and/or its hydrate and/or the total concentration in the range of from 2.5 to 40% by weight based on the total weight of the composition. Or its salt. A hair straightening composition according to any one of claims 1 to 6, which has a pH of from 1 to 3. The hair straightening composition according to any one of claims 1 to 7, wherein the polymeric thickener is selected from the group consisting of a nonionic polymer, an anionic polymer, an amphoteric polymer, and a tertiary or quaternary ammonium group. a cationic polymer. The hair straightening composition of any one of claims 1 to 8, wherein the polymeric thickener does not contain a primary amine group. The hair straightening composition according to any one of claims 1 to 9, wherein the polymeric thickener is selected from the group consisting of methyl hydroxyethyl cellulose (MHEC) and methyl ethyl hydroxyethyl cellulose (MEHEC). Nonionic polymer. The hair straightening composition according to any one of claims 1 to 9, wherein the polymeric thickener is an anionic polymer selected from the group consisting of tristancene, hydroxypropyltrisin and dehydrogenosene. The hair straightening composition according to any one of claims 1 to 9, wherein the polymeric thickener is selected from the group consisting of polytetra-ammonium-37 and polytetra-ammonium-22. The hair straightening composition of any one of claims 1 to 12, wherein the composition comprises at least one surfactant selected from the group consisting of nonionic, anionic, cationic and amphoteric surfactants. A hair straightening composition according to claim 13 wherein the composition comprises a cationic surfactant. A hair straightening composition according to any one of claims 1 to 14, which is an emulsion. A hair straightening composition according to claim 15 which comprises at least one higher alcohol having from 8 to 22 carbon atoms. The hair straightening composition of any one of claims 1 to 16, further comprising polyfluorene. A hair straightening composition according to any one of claims 1 to 17, which contains less than 2 wt.% of a sulfur-based reducing agent. The hair straightening composition of claim 18, wherein the straightening composition does not contain a sulfur-based reducing agent. A use of a hair straightening composition according to any one of claims 1 to 19 for straightening hair. The use of claim 20, wherein the hair straightening composition is not used in combination with a reducing composition or an alkali relaxing agent. A method for semi-permanent hair straightening comprising the steps of: (a) applying a hair straightening composition according to any one of claims 1 to 19 to the hair; (b) making the combination Leave the hair on the hair for 1 to 120 minutes; (c) rinse the hair as appropriate; (d) dry the hair; (e) have a surface having a range of 180 ± 50 ° C, preferably 170 to 200 ° C A hair iron is used to treat the hair; and (f) the hair is rinsed and/or shampooed as appropriate and dried. The method of claim 22, wherein the combination with the administration of the reducing composition or the base relaxant is excluded. The method of claim 22 or 23, wherein in step (b), the hair is straightened and combined Leave the hair on the hair for 10 to 60 minutes. A kit for hair straightening comprising the hair straightening composition of any one of claims 1 to 19 and a straightening iron.